Control of a Chiral Property of a Calix[3]aramide: The Racemization Suppressed by Intramolecular Cyclic Hydrogen Bonds and DMSO鈥揌2O System-Induced Spontaneous Resolution

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• 作者：Kosuke Katagiri ; Shinsuke Komagawa ; Masanobu Uchiyama ; Kentaro Yamaguchi ; Isao Azumaya
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：August 7, 2015
• 年：2015
• 卷：17
• 期：15
• 页码：3650-3653
• 全文大小：290K
• ISSN：1523-7052

文摘

A calix[3]aramide has been synthesized bearing three triphenylphosphinic amide moieties, which formed intramolecular cyclic hydrogen bonds that suppressed its cone/partial cone inversion. The intramolecular cyclic hydrogen bonds were disrupted by DMSO, and the insertion of H₂O into the hydrogen bonds triggered the spontaneous resolution of the calix[3]aramide. Within a chiral environment, such as that afforded by the presence of optically active 2-butanol, the calix[3]aramide underwent a symmetry breaking crystallization process.